Dimethyl 4-fluoro-2-nitrophenylmalonate → 2-(4-Fluoro-2-nitrophenyl)acetic acid

HRID 2121396Notes

Reaction equation

HRID 2121396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](C(OC)=O)[C:9]([O:11]C)=[O:10])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.C(OCC)(=O)C.CCCCCC>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 9838325Dimethyl 4-fluoro-2-nitrophenylmalonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 107504922-(4-Fluoro-2-nitrophenyl)acetic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dimethyl 4-fluoro-2-nitrophenylmalonate (5.0 g) was refluxed in 20 mL of 6N hydrochloric acid for 24 hours. The reaction was cooled and the white solid collected by vacuum filtration, washed with water and dried to give 3.3 g (87% yield) of 4-fluoro-2-nitrophenylacetic acid, Rf 0.6 on thin layer chromatography (ethyl acetate:hexane 1:2, silica gel).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe white solid collected by vacuum filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2691fcdf03124c2fbe3002174ffba444
Source dataset
uspto-grants-2004_02
Patent number
US06696448B2

Reaction notes

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